3-(1',1'-dimethylallyl)-3-(3",3"-dimethylallyl)-1,2,3,4-tetrahydro-2,4-quinoldione | 84017-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(1',1'-dimethylallyl)-3-(3",3"-dimethylallyl)-1,2,3,4-tetrahydro-2,4-quinoldione
• 英文别名: buchapsine；buchapine；3-(2-methylbut-3-en-2-yl)-3-(3-methylbut-2-enyl)-1H-quinoline-2,4-dione
• CAS: 84017-97-0；101143-93-5
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: LAXFAGHIJVQGNK-UHFFFAOYSA-N

物化性质

• 沸点：
  443.2±34.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1',1'-dimethylallyl)-3-(3",3"-dimethylallyl)-1,2,3,4-tetrahydro-2,4-quinoldione 以 various solvent(s) 为溶剂， 反应 3.0h， 以47%的产率得到3-(3-甲基-2-丁烯-1-基)-4-[(3-甲基-2-丁烯-1-基)氧基]-2-喹啉醇
  参考文献：
  名称：

  3-（3,3-二甲基烯丙基）-4-（3,3-二甲基烯丙氧基）喹啉-2-酮的可逆克莱森重排；布查宾的合成及其1，1-二甲基烯丙基的丢失

  摘要：

  3-（3,3-二甲基烯丙基）-4-（3,3-二甲基烯丙氧基）喹啉-2-酮（5）的可逆Claisen重排提供了生物碱布查宾（6），后者很容易失去1,1-二甲基烯丙基基团; 提出了裂解反应的机理。

  DOI：

  10.1016/s0040-4039(00)99007-5
• 作为产物：
  描述：

  3-(3-甲基-2-丁烯-1-基)-4-[(3-甲基-2-丁烯-1-基)氧基]-2-喹啉醇 在 sodium acetate 作用下， 以 乙酸酐 为溶剂， 反应 12.0h， 以56%的产率得到3-(1',1'-dimethylallyl)-3-(3",3"-dimethylallyl)-1,2,3,4-tetrahydro-2,4-quinoldione
  参考文献：
  名称：

  Synthesis of the Quinoline Alkaloids Buchapine and Ravesilone

  摘要：

  DOI：

  10.3987/r-1986-07-1821

文献信息

• 4-Hydroxycoumarin and Related Systems: Sitoselectivity of the Mitsunobu Reaction with Prenyl Alcohols
  作者：Giancarlo Cravotto、Gian Mario Nano、Giovanni Palmisano、Silvia Tagliapietra

  DOI：10.3987/com-03-9737

  日期：——

  The Mitsunobu reaction leads to the formation of new C-C bonds between prenyl alcohols and 1,3-dicarbonyl compounds like 4-hydroxycoumarin or its nitrogen isoster. Buchapine was obtained through a one-pot procedure from 4-hydroxy-2-quinolone and dimethylallyl alcohol.
• Synthesis and anti-HIV activity of alkylated quinoline 2,4-diols
  作者：Nafees Ahmed、Keyur G. Brahmbhatt、Sudeep Sabde、Debashis Mitra、Inder Pal Singh、Kamlesh K. Bhutani

  DOI：10.1016/j.bmc.2010.03.015

  日期：2010.4

  Naturally occurring quinolone alkaloids, buchapine (1) and compound 2 were synthesized as reported in literature and evaluated for anti-HIV potential in human CD4+ T cell line CEM-GFP, infected with HIV-1(NL4.3) virus by p24 antigen capture ELISA assay. The compounds 1 and 2 showed potent inhibitory activity with IC50 value of 2.99 and 3.80 mu M, respectively. Further, 45 alkylated derivatives of quinoline 2,4-diol were synthesized and tested for anti-HIV potential in human CD4+ T cell line CEM-GFP. Among these, 13 derivatives have shown more than 60% inhibition. We have identified three most potent inhibitors 6, 9 and 23; compound 6 was found to be more potent than lead molecule 1 with IC50 value of 2.35 mu M and had better therapeutic index (26.64) as compared to AZT (23.07). Five derivatives 7, 19a, 19d, 21 and 24 have displayed good noticeable anti-HIV activity. All active compounds showed higher CC50 values which indicate that they have better therapeutic indices. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of the Quinoline Alkaloids Buchapine and Ravesilone
  作者：Aurora Bellino、Pietro Venturella

  DOI：10.3987/r-1986-07-1821

  日期：——
• A reversible claisen rearrangement of 3-(3,3-dimethylallyl)-4-(3,3-dimethylallyloxy)quinolin-2-one; synthesis of buchapsine and loss of its 1,1-dimethylallyl group
  作者：Michael F. Grundon、V.N. Ramachandran

  DOI：10.1016/s0040-4039(00)99007-5

  日期：1985.1

  Reversible Claisen rearrangement of 3-(3,3-dimethylallyl)-4-(3,3-dimethylallyloxy)quinolin-2-one (5) furnished the alkaloid, buchapsine (6), which readily lost the 1,1-dimethylallyl group; a mechanism for the cleavage reaction is proposed.

  3-（3,3-二甲基烯丙基）-4-（3,3-二甲基烯丙氧基）喹啉-2-酮（5）的可逆Claisen重排提供了生物碱布查宾（6），后者很容易失去1,1-二甲基烯丙基基团; 提出了裂解反应的机理。

表征谱图